Patent GB-514637-A (GB)
Title: Manufacture of dyestuffs of the anthraquinone series
IPC: C09B1/34
Filed: 1938-05-11
Abstract: 514,637. Dyes and intermediates; dyeing and printing. SOC. OF CHEMICAL INDUSTRY IN BASLE. May 11, 1938, No. 14064. Convention date, May 11, 1937. [Classes 2 (iii) and 15 (ii)] Dyestuffs of the anthraquinone series are manufactured by causing an anthraquinone of the general formula which may contain sulphonic acid groups and in which each X is hydrogen or a hydrocarbon residue, to react with a chrysene or pyrene derivative which contains a hydroxy or amino group and may be further substituted, and, if desired, treating the product with a sulphonating agent, e.g., sulphuric acid monohydrate or fuming sulphuric acid. Suitable starting materials are on the one hand 1-alkylamino-4- halogenanthra quinones and 1-amino-4-halogenanthraquinone-2-sulphonic acids, and on the other hand hydroxypyrene-sulphonic acids, hydroxy-chrysenesulphonic acids, aminopyrenes, aminopyrene-sulphonic acids, amino-chrysenes, diaminochrysenes, amino-and diaminochrysenesulphonic acids. The condensation is preferably effected by heating the reactants in aqueous or aqueous alcoholic solution in the presence of an acid-binding agent, e.g., sodium bicarbonate or caustic soda lye,: and a catalyst facilitating the splitting off of hydrogen halide, e.g., copper bronze or a copper salt. The products may be used for dyeing or printing animal fibres, e.g., wool or silk. In examples: (1) 1-methylamino-4-bromanthraquinone is heated with 3-aminopyrene (obtained by nitrating pyrene and reducing the product), in amylalcohol in the presence of sodium acetate and copper acetate, and the product is stirred with sulphuric acid monohydrate ; the product dyes wool in an acid bath olive-green shades ; (2) sodium-1-amino-4- bromanthraquinone - 2 - sulphonate is heated with the sodium salt of 3-aminopyrenemonosulphonic acid (obtained by sulphonating 3-aminopyrene), in aqueous solution in the presence of sodium bicarbonate and cuprous chloride, yielding a water-insoluble product dyeing wool violet shades and a water-soluble product dyeing wool yellowish-green shades ; (3) sodium 1-amino-4-bromanthraquinone - 2 - sulphonate is reacted as in (2) with the potassium salt of 3-hydroxypyrenemonosulphonic acid (obtained from 3-hyrdoxy-pyrene and chlorosulphonic acid in nitrobenzene), yielding products which dye wool violet and orangebrown shades respectively ; (4) sodium 1- amino-4-bromanthraquinone-2-sulphonate is heated with 3-aminopyrene in aqueous alcohol in the presence of sodium bicarbonate and cuprous chloride (green shades) ; the 3- aminopyrene may be replaced by 2-aminochrysene or 2 8-diaminochrysene (violet to Bordeaux shades) ; (5) sodium 1-amino-4- bromanthraquinone-2-sulphonate is reacted as in (2) with the sodium salt of 2-aminochrysenemonosulphonic acid (obtained by sulphonating 2-aminochrysene) yielding products dyeing wool violet and blue-green shades respectively ; (6) the sodium salt of 2-hydroxychrysenesulphonic acid (obtained from 2-hydroxychrysene -and chlorosulphonic acid in nitrobenzene) similarly yields products dyeing wool violet and orange-brown shades respectively ; (7) wool is dyed blue-green shades with the water-soluble product of (5) in a bath containing Glauber's salt and sulphuric acid.